Process for protecting a substrate with an n4-triazolylaminoarylsulfonamide intumescent agent

ABSTRACT

1. INTUMESCENT COMPOSITIONS OF THE INVENTION COMPRISE CERTAIN N4-TRIAZOLYLAMINOARYLSULFONAMIDES, SUCH AS THE N4TRIAZOLYLSULFANILAMIDES AND DERIVATIVES THEREOF. THE INTUMESCENT AGENTS MAY BE EMPLOYED IN CONJUNCTION WITH ADDITIVES CONVENTIONALLY USED IN INTUMESCENT COMPOSITIONS. FOR USE IN PROTECTING SUBSTRATES FROM HEAT AND FIRE, THE INTUMESCENT COMPOSITIONS MAY BE APPLIED IN ANY SUITABLE MANNER, SUCH AS BY ELECTRODEPOSITION, SPRAYING ONTO AN ADHESIVE SUBSTRATE, OR APPLICATION OF A COATING COMPOSITION COMPRISING THE INTUMESCENT AGENT.

United ittesnruna FOR MISSING xn 3,783,018 PROCESS FOR PROTECTING A SUBSTRA E WITH AN N -TRIAZOLYLAMINOARYLSULFO AMIDE INTUMESCENT AGENT Shirley H. Roth, Highland Park, N.J., assignor to Cities Service Company, New York, N.Y. No Drawing. Filed Feb. 28, 1972, Ser. No. 230,101 Int. Cl. C09d 5/18; C09k 3/28 U.S. Cl. 117-436 5 Claims ABSTRACT OF THE DISCLOSURE BACKGROUND OF THE INVENTION 7' Field of the invention This invention relates to intumescent compositions and more particularly relates to such compositions containing a one-component intumescent agent.

Description of the prior art It is known that a substrate may be protected from heat and tire by the application of an intumescent composition. Intumescent compositions of the prior art usually contain an intumescent agent having at least three components; i.e., a carbonific, a spumific, and a catalyst; and they are typically characterized by the disadvantages of high cost, low spreading rate, relatively poor efficiency, poor water resistance, and poor weatherability.

As disclosed in US. Pat. 3,535,130, it has already been discovered that a one-component intumescent agent has advantages over multicomponent intumescent agents. However, the intumescent agents of the patent have poor adherence to substrates and have an undesirable degree of moisture sensitivity.

SUMMARY OF THE INVENTION wherein Ar is a divalent aromatic residue, R is a triazolyl or substituted triszolyl radical. and R is hydrogen, hydrocarbon, substituted hydrocarbon, or acyl.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The intumescent agents of the invention may be any compounds corresponding to the above formula. However, they are preferably compounds wherein Ar is a divalent aromatic residue derived from benzene or naphthalene or an alkyl, hnlonlkyl, allcoxy, haloalkoxy, halo, hydroxy, c'nrboxy, amino, amido,or nitro derivative there- SEARCH ROOM Patented Jan. 1, 1974 "a of. When the aromatic ring bears organic substituents, it l) v is usually preferred that these substitutents contain 1-5 carbon atoms. When there are halo substituents, it isQ- t usually preferred that they be chloro or bromo. It is also a preferred that the aromatic ring have at least one free reactive position.

R of the above formula is frequently a triazolyl radical, but it may be substituted if desired. The substituted triazolyl radicals most commonly found in these compounds are the chloro, bromo, carboxy, hydroxy, amino, thio, sulfonamido, C -C alkyl, C -C alkoxy, phenyl, and benzo derivatives, but compounds containing other substituted triazolyl radicals are also utilizable. When R is a substituted triazolyl radical, the nitrogen of the ar-arnino group may be attached directly to the triazole ring, or it may be attached to the ring through the substituent.

As indicated above, R may be hydrogen or a hydrocarbon, substituted hydrocarbon, or acyl radical, preferably hydrogen or a C -C alkyl, phenyl, aminophenyl, sulfonamidophenyl, nitrophenyl, or acetyl radical.

Exemplary of the intumescent agents of the invention are N -1,2,3-triazol-l-ylsulfanilamide, N -1,2,4-triazol-4-ylsulfanilamide, N -1,2,4-tria2ol-3-ylsulfanilamide, N -l,2,5-triozol-3-ylsulfanilamide, N 1 ,3,4-triazol-2-ylsulfanil amide, 4-(1,2,4-triazol-3-yl)amino-3-chloro-benzenesulfonamide, 2-(1,2,4-triazol-4-yl)amino-4-bromo-benzenesu1fonamide, 4-(1,2,4-tri.azol-3-y1)amino-Z-ethyl-benzenesulfonamide, 3-(1,2,4-triazol-3-yl)amino-4-chloro-methylbenzenesulfonamide, 4-(1,2,4-triazol-3-yl)amino-2-butoxybenzenesulfonamide, 4(1,2,3-triazol-4-yl)amino-3 chloromethoxybenzene sulfonomide, 4- 1,2,3 -triazol-1-yl -amino-3-hydroxybenzenesulfonamide, 4-(1,2,3-triazol-1-yl)-amino3-carboxybenzenesulfonamide, 4-(1,2,4-triazol-4-yl)-amino-3-aminobenzenesulfonamide, 4-(1,2,4-triazoi-3-yl)-amino-2-acetamidobenzenesulfonamide, 2-(1,2,5-triazol-3-yl)amino-4-nitrobenzenesulfonamide, N -(S-chloro-l ,2,4-triazol-2-yl sulfonilamide, N -(3-bromo-1,2,4-triazol-4-yl)-sulfanilamide, N -(5-ethylcarboxy-1,2,3-triazol-1-yl)-sulfanilamide, N 4-h ydroxyl ,2,5-triazol-3-yl sulfanil amide, N 5-amino-1,3,4-triazol-2-yl sulfanilamide, N (S-methylthio-l,2,4-triazol-3-yl sulfanilamide, N ,N -1,2,4-triazol-3,5-yl bis-sulfanilamide, N -(3methyl-1,2,4-triazol-5-yl) sulfanilamide, N (5-ethoxy-l,2,4-triazol-3-yl)sulfanilamide, N S-phenyl-l ,2,4-triazol-3-yl -sulfanilamide, N -benzotriazol-7-ylsulfanilamide, N -benzotriazol-d-ylsulfanilamide,

N -ethyl-N -1,2,4-triazol-3-ylsulfanilamide,

N -(4-aminophenyl) -N -l,2,4-triazol-3-ylsulfanilamide,

N -(4-sulfonamidophenyl)-N -1,2,4-triazol-3-ylsulianilamide,

N (4-nitrophenyl -N -l,2,4-triazol-3-ylsulfanilamide,

N -acetylN*-1,2,4-triazol-3-ylsulfanilamide,

the corresponding naphthalene compounds, etc. When not readily available, these compounds may be prepared by known techniques.

For use in protecting a substrate from heat and tire, the intumcscent agents of the invention may be applied in any suitable manner, cg, electrodeposition, spraying of pow dered intumescent agent onto an adhesive substrat etc.

However, it is usually preferred to compound the intumescent agent with a binder, e.g., nitrocellulose, and optionally also with one or more of the other ingredients conventionally used in intumescent compositions, e.g., stabilizers, dispersing agents, pigments, driers, biocides, anti-foamers, thickeners, protective colloids, fillers, blowing agents, etc.; disperse the composition in a suitable liquid medium, e.g., water or a solvent or solvent mixture; and apply the coating composition thus formed to the substrate to be protected. As is the case with conventional intumescent coating compositions, it is frequently convenient to apply these coating compositions in the form of a paint having a solids content of about 10-70% by weight and an intumescent agent/binder weight ratio of about 0.075-14/1 to deposit a coating having a dry thickness of about 0.001- 0.75 inch.

The intumescent agents of the invention are efficient, have low moisture sensitivity, and intumesces to form foams having good volume, cell structure, and adherence tov substrates, such as wood, metal, and plastics. They are also useful as flame retardants in normally flammable compositions.

The following example is given to illustrate the invention and is not intended as a limitation thereof.

EXAMPLE I Place one gram of N 1 1,2,4 triazol-3-ylsulfanilamide in an alumiunm pan and flame it with a propane torch. The compound intumesces to form an excellent volume of foam having a good cell structure.

Similar results are obtained when the other intumescent agents mentioned in the specification are substituted for the intumeseent agent of the example.

It is obvious that many variations may be made in the products and processes set forth above without departing from the spirit and scope of this invention.

What is claimed is:

1. A process for protecting a substrate from heat and fire which comprises applying thereto an intumescent composition comprising as the intumescent agent a compound corresponding to the formula:

References Cited UNITED STATES PATENTS 2,369,949 2/1945 DAlelio 260--239.9 3,535,130 10/1970 Webb ll7136 X 3,663,464 5/1972 SaWkO 117l36 X 3,707,554 12/1972 Hardy 117-136 X FOREIGN PATENTS 583,367 12/1946 Great Britain 260-2399 WILLIAM D. MARTIN, Primary Examiner H. J. GWINNELL, Assistant Examiner US. Cl. X.R. 10615 FP 9 233 UNITED S'JTA'IES MTEN'I OFFICE CERTIFKQATE 01; CGHREQTEON Patent 1791018 Dated January 1 1974 Inventor (s) Shir1ey H. ROCh It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Co1umn 2, 1ine 2 "substitutents" shou1d read substi tuents 1 co1umn 2, 1ine 27, the portion of the word reading "triozo1 shou1 d read triaz01 co1umn 2, 1ine 47, the portion of the word reading "su1foni1amide" shou1d read su1fani1amide C01 umn 3, 1 ine 18, "intumesces" shou1d read intumesce co1umn 3, 1ine 27 "a1 umiunm" shou1d read a1uminum Co1umn 4, 1ine 5, the portion of the formu1a reading R" shou1d read R' Signed and sealed this 23rd day of April 1971+.

(SEAL Attest:

EDWMiD PLFLETCHER TR. C. MARSHALL DANN Atte sting Officer Commissioner of Patents 

1. INTUMESCENT COMPOSITIONS OF THE INVENTION COMPRISE CERTAIN N4-TRIAZOLYLAMINOARYLSULFONAMIDES, SUCH AS THE N4TRIAZOLYLSULFANILAMIDES AND DERIVATIVES THEREOF. THE INTUMESCENT AGENTS MAY BE EMPLOYED IN CONJUNCTION WITH ADDITIVES CONVENTIONALLY USED IN INTUMESCENT COMPOSITIONS. FOR USE IN PROTECTING SUBSTRATES FROM HEAT AND FIRE, THE INTUMESCENT COMPOSITIONS MAY BE APPLIED IN ANY SUITABLE MANNER, SUCH AS BY ELECTRODEPOSITION, SPRAYING ONTO AN ADHESIVE SUBSTRATE, OR APPLICATION OF A COATING COMPOSITION COMPRISING THE INTUMESCENT AGENT. 